Hydrochloric Acid → HCID 71736100, compound

HRID 1481140Notes

Reaction equation

HRID 1481140 reaction equation
C[O:2][C:3](=[O:31])[C:4]([CH3:30])([CH3:29])[CH2:5][NH:6][C:7]([C:9]1[N:10]=[C:11]([C:27]#[N:28])[C:12]2[C:17]([C:18]=1[OH:19])=[CH:16][C:15]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:14][CH:13]=2)=[O:8].[OH-].[Na+].Cl>CO>[C:27]([C:11]1[C:12]2[C:17](=[CH:16][C:15]([O:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:14][CH:13]=2)[C:18]([OH:19])=[C:9]([C:7]([NH:6][CH2:5][C:4]([CH3:30])([CH3:29])[C:3]([OH:31])=[O:2])=[O:8])[N:10]=1)#[N:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 89812874HCID 89812874, compound

Product 1

HCID 71736100HCID 71736100, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-[(1-cyano-4-hydroxy-6-phenoxy-isoquinoline-3-carbonyl)-amino]-2,2-dimethyl-propionic acid methyl ester (38 mg, 0.091 mmol), 2 M NaOH (2 mL) and MeOH (2 mL) was stirred at r.t. for 3 h. 1 M HCl was added until pH was ˜2, and the resulting suspension was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography (0-25% EtOAc/hexanes+2% AcOH) to give 20 mg of the title compound. MS: (−) m/z 404.11 (M−1).

Workup

  1. extractionthe resulting suspension was extracted with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography (0-25% EtOAc/hexanes+2% AcOH)

Sources & evidence

ORD record
ord-306c746c54f14547b3fcaccd844dc2d8
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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